Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 26.3, Problem 6P
What
(a) Leucine
(b) Histidine
(c) Tryptophan
(d) Methionine
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Indicate whether each statement is true or false. (a) Tryptophan is an aromatic amino acid. (b) Lysine is positively charged at pH 7. (c) Asparagine has two amide bonds. (d) Isoleucine and leucine are enantiomers. (e) Valine is probably more water-soluble than arginine.
α-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis.
What amino acid is formed when the aldehyde that is used is 3-methylbutanal?
(a) Predict the product of the reaction of KOH with 1-amino propane.
(b) Predict the product of a deprotonated ethanol (an “ethanolate anion", O-CH2-CH3)
with phenol (hydroxybenzene).
(c) Predict the product of propanoic acid with deprotonated ethanol (an “ethanolate
anion", O-CH2-CH3).
Chapter 26 Solutions
Organic Chemistry
Ch. 26.1 - How many of the -amino acids shown in Table 26-1...Ch. 26.1 - Prob. 2PCh. 26.1 - Prob. 3PCh. 26.2 - Hemoglobin has pI=6.8. Does hemoglobin have a net...Ch. 26.3 - Show how you could prepare the following -amino...Ch. 26.3 - What alkyl halides would you use to prepare the...Ch. 26.3 - Prob. 7PCh. 26.4 - There are six isomeric tripeptides that contain...Ch. 26.4 - Draw the structure of M-P-V-G, and indicate its...Ch. 26.5 - Prob. 10P
Ch. 26.5 - Prob. 11PCh. 26.6 - The octapeptide angiotensin II has the sequence...Ch. 26.6 - Prob. 13PCh. 26.6 - Prob. 14PCh. 26.6 - Give the amino acid sequence of hexapeptides that...Ch. 26.7 - Prob. 16PCh. 26.7 - Write all five steps required for the synthesis of...Ch. 26.10 - Prob. 18PCh. 26.SE - Identify the following amino acids:Ch. 26.SE - Prob. 20VCCh. 26.SE - Isoleucine and threonine are the only two amino...Ch. 26.SE - Prob. 22VCCh. 26.SE - Give the sequence of the following tetrapeptide:Ch. 26.SE - Prob. 24MPCh. 26.SE - The chloromethylated polystyrene resin used for...Ch. 26.SE - Prob. 26MPCh. 26.SE - Prob. 27MPCh. 26.SE - Prob. 28MPCh. 26.SE - Except for cysteine, only S amino acids occur in...Ch. 26.SE - Prob. 30APCh. 26.SE - Prob. 31APCh. 26.SE - Show the structures of the following amino acids...Ch. 26.SE - Prob. 33APCh. 26.SE - Using both three- and one-letter codes for amino...Ch. 26.SE - Prob. 35APCh. 26.SE - Show how you could use the acetamidomalonate...Ch. 26.SE - Prob. 37APCh. 26.SE - Show how you could prepare the following amino...Ch. 26.SE - Prob. 39APCh. 26.SE - Predict the product of the reaction of valine with...Ch. 26.SE - Prob. 41APCh. 26.SE - Prob. 42APCh. 26.SE - Propose two structures for a tripeptide that gives...Ch. 26.SE - Show the steps involved in a synthesis of...Ch. 26.SE - Prob. 45APCh. 26.SE - Prob. 46APCh. 26.SE - Prob. 47APCh. 26.SE - Which of the following amino acids are more likely...Ch. 26.SE - Leuprolide is a synthetic nonapeptide used to...Ch. 26.SE - The -helical parts of myoglobin and other proteins...Ch. 26.SE - Prob. 51APCh. 26.SE - Cytochrome c is an enzyme found in the cells of...Ch. 26.SE - Prob. 53APCh. 26.SE - Prob. 54APCh. 26.SE - Prob. 55APCh. 26.SE - What is the structure of a nonapeptide that gives...Ch. 26.SE - Oxytocin, a nonapeptide hormone secreted by the...Ch. 26.SE - Aspartame, a nonnutritive sweetener marketed under...Ch. 26.SE - Prob. 59APCh. 26.SE - Prob. 60APCh. 26.SE - Prob. 61APCh. 26.SE - Prob. 62AP
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- Phospholipids undergo saponification much like triglycerides. Draw the structure of a phospholipid meeting the followingcriteria. Then draw the products that would result from its saponification.(a) a cephalin containing stearic acid and oleic acidarrow_forwardBoth norepinephrine and epinephrine are synthesized from the same protein-derived amino acid. From which amino acid are they synthesized? What types of reactions are involved in their biosynthesis? н он H OH H HO. NH, НО. CH3 (a) (b) HO НО Norepinephrine Epinephrine (Adrenaline)arrow_forwardDraw structural formulas for the following compounds: (a) Tributylamine(b) N-methylanilinium chloride(c) ethylammonium chloride (d) 2-amino-1-pentanol(e) 3,3-dimethyl-N-phenyl-2-aminohexane (f) 1,2-ethanediaminearrow_forward
- α-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis. What aldehyde is needed to prepare isoleucine?arrow_forwardA chemically modified guanidino group is present in cimetidine (Tagamet), a widely prescribed drug for the control of gastric acidity and peptic ulcers. Cimetidine reduces gastric acid secretion by inhibiting the interaction of histamine with gastric H2 receptors. In the development of this drug, a cyano group was added to the substituted guanidino group to alter its basicity. Do you expect this modified guanidino group to be more basic or less basic than the guanidino group of arginine? Explain.arrow_forwardDraw the structure of the phenylthiohydantoin derivatives of(a) alanine. (b) tryptophan. (c) lysine. (d) proline.arrow_forward
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